Diethyl Ether → HCID 57671757, compound

HRID 1182766Notes

Reaction equation

HRID 1182766 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[I:10]N1C(=O)CCC1=O.C(OCC)(=O)C.C(OCC)C>CN(C)C=O>[OH:9][C:5]1[CH:6]=[CH:7][C:8]([I:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 90073-MethoxyphenolHCID 120273N-Iodosuccinimide

Product 1

HCID 57671757HCID 57671757, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-methoxyphenol (600 mg, 4.83 mmol) and N-iodosuccinimide (1.09 g, 4.84 mmol) was dissolved in anhydrous N,N-dimethylformamide (25 mL), and the mixture was stirred at room temperature overnight. Ethyl acetate (100 mL) and diethylether (100 mL) were added. The organic layer was washed with 1% aqueous sodium thiosulfate solution (200 mL), water (100 mL), and saturated brine (50 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (167 mg) as a colorless oil. (Yield 14%)

Workup

  1. washThe organic layer was washed with 1% aqueous sodium thiosulfate solution (200 mL), water (100 mL), and saturated brine (50 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-dd0810146f5b4dee86e7c91839d28338
Source dataset
uspto-grants-2014_03
Patent number
US08664221B2

Reaction notes

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